My 'Under the Tuscan Sun' Tinder Disaster

The idea was almost as bad as the movie. I had some time off work and was in a dark place, so I decided to travel alone to Tuscany. My personal version of Under the Tuscan Sun, the cheesy Diane Lane movie from 2003. Because when planning an expensive vacation, the first thing you should ask is, "What's the funniest option?" I wasn't a middle-aged divorcée heading to Italy to rediscover myself and tan the skin where my wedding ring used to be, but I was single, emotionally lost, and riddled with the disease you get from cleaning litter boxes where you're disturbingly attached to your cats. So… close enough. Everyone around me was meeting their soulmate or having their second kid, and I was impersonating Diane Lane. I packed a sunhat and fled to Italy.

Desperate for human connection of any kind, I made a rash decision: I'd leave Tuscany early and head back to Rome to Tinder my face off.

The first three days were glorious. I wandered around Rome, rented a car, and headed north to wine country. I was relaxed, open, and falling in love with me again—the whole movie thing was working! I soon realized that three days was the maximum amount of time I could spend alone and enjoy myself. After that, I began unraveling. As I drove from town to town in the most romantic place on Earth, filled with couples and retired groups of friends from Texas (all married!), I couldn't believe I had done this. No one else in Tuscany could either. Hotel concierges walked me to my rooms, confused. Restaurant hosts led me to romantic tables for two, horrified. Waiters insisted on taking the second table setting away, as if to signal to everyone that no one would ever be coming to join me.

The days under the Tuscan sun were long. Even if I woke up, had a leisurely breakfast, meditated, read, drove to a town, and wandered every corner of it, it would still only be 11:30am. "Maybe I'll die today," I'd think. "That would suck up some time." But death wasn't even a possibility. If I steered my car off the road, it would just glide down a pristine hillside, crashing into nothing. I finished three books but couldn't tell you the plot of any of them. All I could focus on were my poor life choices that led me to this vacation.

Desperate for human connection of any kind, I made a rash decision: I'd leave Tuscany early and head back to Rome to Tinder my face off. After swiping left on 7,000 shirtless men named Andrea, I matched with Marco, a photojournalist and diplomat from Verona (romantic!). He sent me YouTube videos of himself being interviewed on local news shows. They were in Italian, so he could have been pitching a sequel to the Holocaust and I wouldn't have known, but, whatever! He looked hot in a suit and I was ready for love.

Marco texted: "What do you want out of this? What happens if we like each other?" "If we like each other, then we have a fun weekend," I answered, cool as shit. My mind was racing. Love was coming! I couldn't wait to parade him back to the States with me and show him off to all my boring friends who married Americans. Thank God I'd been so miserable in Tuscany, I needed to be sad to fully appreciate this happiness. Life is a cycle.

He texted again. He was very into me. "Do you have limits?" Suddenly, we were having a different conversation. From there, it derailed fast. "Do you have shave pussy? I want to fuck you with shave pussy." Normally that would be my cue to un-match, but I was so disillusioned with my version of Under the Tuscan Sun, I decided to "yes and" it. The trip couldn't get worse, and I needed a better story than, "I drove around wine country feeling sorry for myself. At night, I drank alone and looked at Facebook pictures of my ex-boyfriends' children." We made a date to meet in Rome on Thursday.

Thursday arrived. A person! I was going to see a person! So what if he was a sex-addict, Holocaust 2 supporter? I was going to spend an evening with a person. I texted him to figure out a plan: Drinks? Dinner? Dancing? He explained that he had dinner plans and wanted to meet at a park at 4 p.m.. Much like my life, this affair continued to not go how I hoped. I put on a great, cute/casual 4 p.m. outfit and headed over. As I approached our meeting spot, I had two equal fears: Fear #1: a van would pull up, a door would slide open, and I would be Taken. This was only a minor fear because I'm too old to be Taken, and you'd have to put me on so many of those sex trafficking drugs to get me down to Taken weight, it wouldn't be worth the investment. Also, I'm an easily dehydrated, whiney Jew. No Saudi Prince would buy me at auction. Fear #2: Marco would see me from across the street and, despite his uncontrollable sexual urges, he'd decide I'm super unfuckable. In this fear, my self-confidence and feminist beliefs were no match for my devastated ego.

Italian men are excellent at convincing you to live in the moment when they want to have sex with you.

Neither of these things happened. We met. He was stunning. He was sweaty from riding his bike, yet he still smelled magnificent. A combination of undeniable manliness and diplomat's cologne? (Note: All over Rome there are statues of naked men. I assumed they were statues of gods, but that's actually what Italian men look like. They're all ripped, hairless, and they have that muscle-y bone thing on the side of their torsos that you don't see on men in comedy.) We strolled through the park. Marco asked a few mandatory personal questions and I did the same, but it was clear there was no need for us to get to know each other. "Where is your hotel?" he asked, two minutes in to meeting. "Let's go there now." He didn't have much time, as he had to prepare for a dinner party I wasn't invited to. "I thought maybe we'd hang out first," I foolishly exclaimed. "You leave in two days, there is no time." (Note: Italian men are excellent at convincing you to live in the moment when they want to have sex with you.) He continued. "It is not a big deal. You are American, you should be open about sex." I was American! I wasn't sure how that related to sexual openness, but maybe he was right?

I considered leaving, but then I remembered: I had no other plans that day, or for the rest of the trip. "Let's hang out for a little longer," I suggested. We walked over to a bench, where he didn't waste a second before grabbing my left breast and cramming his tongue so far down my throat, it wasn't possible to kiss back. Reminder: it was 4:03 p.m. on a weekday in a touristy park. Children were passing by in pedicabs, an old woman walked by and locked eyes with me as I came up for air. She glared at me and I wanted to yell, "I know I'm being repulsive, but you have to understand: I was just alone in Tuscany!"

We undressed. Thus began the most disappointing sex I have ever had.

"So?" Marco asked. The kiss wasn't going in the pro-column, but I had already eaten carbonara and toured the Forum, why not add this to the itinerary? "I won't have unprotected sex," I declared, my self-respect bursting to the surface. He nodded in agreement. "Okay then. We will go back to your hotel, we will give each other oral sex, and we will have sex with a condom." I shrug-nodded. I was going to see this through.

Minutes later, we arrived at my hotel. Marco excused himself to go to the bathroom, probably to wash his dick. I quickly tidied up the room. Not sure why. If my Converse were on the floor, I bet he still would've been down to fuck (Hey Converse, want to sponsor my next vacation?). When he resurfaced, I opened the mini-fridge. "Champagne?" I offered. "No." Why even pretend this is a romantic encounter? We undressed. Thus began the most disappointing sex I have ever had.

Marco was assertive, which can be a turn-on, but his brand of assertiveness felt selfish and misogynistic. Or, perhaps I was too old to be commanded to lick a stranger's balls. In the absence of sexual enjoyment, my mind went adrift. I thought about the girl from Fifty Shades of Grey and realized that she definitely wasn't Jewish. If she were, the affair would have lasted ten minutes and it would have been my favorite book of all time. "You want me to what?! I'm gonna call an Uber." By the time I tuned back in, Marco was (thankfully) finishing up. "I want to come in your face," he whispered. Surely, this was a lapse in his English. "You want to come in my mouth?" I asked, as if that were a preferable alternative. He didn't answer, he just pulled out and began positioning himself toward my head. I squirmed, but he was too ambitious. I lost the negotiation. Turns out, Marco did want to come on my face. On every part of my face. There was so much cum, if I cared about him at all, I would have suggested he go to the hospital. "Sorry," he shrugged. "I'm a very visual guy." "Can you visualize me a towel? Because I can't see right now."

In a triumph of feminism, I didn't apologize.

Next, in what was probably the biggest surprise of the afternoon, he spooned me. Not sure why he bothered with affection at that point. I had never wanted a person to hold me less. And what were we possibly going to talk about? Luckily, Marco had a topic: "Do you like cuckolding?" "Um…in what sense?" "Would you want to have sex with another man while I watch? Maybe tomorrow?" Many questions came to mind, but "Are you bisexual?" is the one I went with. He sat up, offended. "Why would you say that?" "Because you want to fuck another guy with me?" "I will not have sex with him. I will just watch. I'm a very visual guy." I got the message, Marco. No need to remind. "Don't think I'd be into that." In a triumph of feminism, I didn't apologize. "How about a woman? I know this girl at my work, she crazy, she think about sex all the time." (Idea: workplace comedy at the Italian government. No one gets anything done because everyone is too horny.) He kept going: "You will like her. She has dragon tattoo on her pussy." Wow, this guy didn't know me at all. I declined. Even if I was interested in that once-in-a-lifetime offer, I was house-sitting for an acquaintance that weekend and I didn't feel comfortable with her coming home to find me dead and covered in an unfathomable amount of cum.

I walked him to the door. Here, he had one final opportunity for romance. "Normally while women give me oral sex I like to take their picture, but I didn't ask you, because I didn't think you'd be into it." Aww, he did know me!

Our lives will be imperfect no matter what we do, so our choices might as well be our own.

If you've never seen Under the Tuscan Sun, I should make it clear that nothing even remotely like that happened. I've often made the mistake of comparing myself to other people. I was nothing like Diane Lane in that movie, or any of the people at home who "got their lives together" before me, whatever that means. I also wasn't Julie Delpy in Before Sunrise (so graceful!), or any woman who can pull off high-waisted jeans or take a yoga class without bailing halfway through. And that's a good thing. Even when my life feels slow-moving, weird, or even humiliating, it is unlike anyone else's. Our lives will be imperfect no matter what we do, so our choices might as well be our own. From now on, I'm going stop living other people's adventures. But first, I want to pull a The Holiday.

Ali Waller is a comedian and writer for the Netflix show Love, which premieres tomorrow, Feb 19.

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